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21 Photos

Castle | 6 Bedrooms | sleeps 16

4 Nights min stay

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from £390 /night

£2728 - £3182 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic castle with pool to rent near Montepulciano – sleeps 14+2 From 3300€ to 3850€ a week  …see more

14 Photos

Farmhouse | 5 Bedrooms | sleeps 9

3 Nights min stay

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from £128 /night

£893 - £1686 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Comfortable country house with private pool to rent near San Casciano dei Bagni – sleeps 9 From 1080€ to 2040€ a week  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

7 Nights min stay

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from £48 /night

£331 - £414 / week

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Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Nicely furnished country style apartment, S. Andrea is part of a restored 15 century Monastery with an antique chapel and a brick courtyard. Located in the historic medieval city of Siena. Peaceful and reserved atmosphere. Private Garden, secure indoor parking, WiFi. 1 hour drive from main Tuscan attractions, Florence, S. Gimignano, Montalcino, Chianti vineyard, Hill towns.  …see more

Featured properties

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Min stay varies

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from £88 /night

£614 - £1402 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £218 /night

£1526 - £2064 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £69 /night

£482 - £701 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Self-catering apartment, very comfortable, three bedrooms, a large living with two comfortable armchairs, and an open well furnished kitchen. Located in a wonderful Tuscan countryside, surrounded by a very large garden and a new pool. Ideal for families.  …see more

4 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £642 /night

£4490 - £6352 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A beautiful villa recently restored with an absolutely fascinating panoramic position; surrounded by Mediterranean vegetation and of vines and olives  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Short stays welcome

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from £151 /night

£1052 - £3505 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
The villa stands independent on the top of a hill and it's ideal for those who want to enjoy the peace of the green Tuscany hills all around the house with a beautiful landscape and wide, superb views.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £99 /night

£690 - £868 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £549 /night

£3843 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Everything about this property is classically Tuscan. Misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with green shutters.  …see more

23 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £496 /night

£3472 - £4629 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £1612 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £142 /night

£992 - £1653 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 19

7 Nights min stay

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from £296 /night

£2067 - £5290 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £107 /night

£744 - £2058 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £176 /night

£1232 - £1645 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £224 /night

£1562 - £3430 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £148 /night

£1034 - £1529 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £473 /night

£3306 - £4877 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa La Torre is a medieval lookout tower, built more than 8 centuries ago on Etruscan foundations, and at a later date incorporated into the farmhouse structure.  …see more

19 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £473 /night

£3306 - £4959 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa La Corte is a large farmhouse from the early 15th century, built around a thousand-year-old lookout Lombard tower and set inside six hectares of private grounds amidst the hills covered in vineyards and olive trees, just outside of San Gimignano.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £101 /night

£703 - £1009 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villino Montisi is a splendid two-story ancient farmhouse surrounded by meadows with breathtaking views over the sweet hills of Tuscany. Recently restored following the architectural Tuscan style with the pale Tuscan stone of the façade.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £272 /night

£1901 - £3058 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The villa is located in a natural reserve and offers walking paths and mountain bike trails, horse riding , historical churches and villas, refreshing dips in the rivers and small lakes.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £414 /night

£2893 - £3926 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3265 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £650 /night

£4546 - £6447 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a secluded parkland in the hills of Tuscany.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £178 /night

£1240 - £1984 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
A cypress tree lined road will lead you to Villino le Tortore and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £222 /night

£1550 - £2149 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Everybody who loves Tuscan tradition, excellent cuisine, biological food and, why not, horse riding and biking, besides a relaxing visit to thermal spas will be enchanted by this area.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 16

Min stay varies

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from £473 /night

£3306 - £4918 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This beautiful farmhouse complex has recently been carefully restored with great attention to detail, so as to combine authentic architectural features and an original rustic style with all modern comforts.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £473 /night

£3306 - £5372 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This elegant villa, with cream-washed external walls, dates back to the late 16th century, when it served as the summer residence and hunting lodge of the noble Tolomei family.  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £123 /night

£860 - £1240 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn.  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £207 /night

£1447 - £2191 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This compact, two-storey, converted Tuscan farmhouse has been extensively renovated, employing in its restoration solely products certified as ecologically friendly.  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £3306 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Demata is the beloved holiday home of a Florentine family with strong American connections as well as a great appreciation for the Tuscan country side and it's pleasures.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £225 /night

£1571 - £2315 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Il Maggio is a typical 18th century Tuscan hill house. The villa offers all modern conveniences and some very particular details including a carefully designed and comfortably furnished solarium with large heated spa bath, a few steps from the house.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £225 /night

£1571 - £2976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £591 /night

£4133 - £4546 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town.  …see more

22 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £271 /night

£1894 - £2581 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Magical Tuscan farmhouse with pool overlooking the stunning Siena countryside. Enjoying the most beautiful and tranquil of settings Le Contessine offers both a relaxing escape and a strategic location for touring the whole of Tuscany and Umbria with ease. 4 bedrooms.  …see more

24 Photos

Villa | 14 Bedrooms | sleeps 27

7 Nights min stay

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from £2630 /night

£18410 - £24546 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £88 /night

£614 - £859 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
We have 5 independent self catering apartments and 2 double rooms with private bathrooms. The apartments have their own kitchenettes inc. oven, fridge and gas hobs. Swimming pool, gardens, outdoor wood oven and BBQ are free to all our guests. We have a restaurant 2 km's from the farmhouse offering tuscan cuisine & Pizza with an outdoor terrace.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £107 /night

£745 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £63 /night

£439 - £614 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Immerse yourself into the authentic Tuscan countryside for a special holiday treat in the middle of olive groves and wineyards with your hosts only too willing to let you taste the produce of such wonders accompoanied by their own home cooking. Whether you choose to stay put, or explore the surrounding countryside and famous sites, Podere La Fonte has the answer for you.  …see more

11 Photos

House | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £62 /night

£430 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Extraordinary typical tuscan historic eighteenth-century residence, all restored, all high standard confort, located on a hilltop in the Siena countryside, in the charming medieval village Sinalunga. You will love your holidays there! Come and live the tuscan way of life : relaxing, friendly, refined.  …see more

11 Photos

Farmhouse | 6 Bedrooms | sleeps 12

Min stay varies

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from £376 /night

£2629 - £3943 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Renaissance Villa with private swimming pool on the Tuscan hills.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £74 /night

£517 - £1034 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
At only ten minutes' drive from Sinalunga town-centre and yet surrounded by peaceful, unspoilt countryside, this fully restored 17th century Tuscan farmhouse combines the best of both worlds.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £63 /night

£439 - £526 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
tuscany farmhouse pool siena florence san gimignano voltera valdelsa chianti wine olive oil art palio uffizi michelangelo  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £517 /night

£3616 - £5682 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa San Biagio is situated close to Montepulciano. This magnificent country house is known for being the most exclusive and stunning farmhouse you can find in this area. It is the perfect choice if you are looking for a peaceful and relaxing holiday.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £555 /night

£3885 - £6529 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills.  …see more

18 Photos

Fort | 1 Bedroom | sleeps 3

Excellent 5/5 

3 Nights min stay

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from £108 /night

£751 - £834 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

22 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £178 /night

£1240 - £2315 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Filippo, is a delicious apartment and it is part of a farmhouse divided in 3 units located close to Montalcino. This apartment can accommodate 6 persons in 3 bedrooms and 2 bathrooms.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1034 /night

£7232 - £12686 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Set on a large estate with extensive views over the Crete Senesi and Siena countryside, this villa is just perfect for family reunions or large group of friends. Built in stone and brick, this Tuscany villa consists of a main villa and a dependence.  …see more